EP0442360B1 - Procédé de transfert de colorants azoiques - Google Patents
Procédé de transfert de colorants azoiques Download PDFInfo
- Publication number
- EP0442360B1 EP0442360B1 EP91101564A EP91101564A EP0442360B1 EP 0442360 B1 EP0442360 B1 EP 0442360B1 EP 91101564 A EP91101564 A EP 91101564A EP 91101564 A EP91101564 A EP 91101564A EP 0442360 B1 EP0442360 B1 EP 0442360B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- alkyl
- radical
- alkoxy
- hydrogen
- transfer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
- B41M5/382—Contact thermal transfer or sublimation processes
- B41M5/385—Contact thermal transfer or sublimation processes characterised by the transferable dyes or pigments
- B41M5/388—Azo dyes
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/913—Material designed to be responsive to temperature, light, moisture
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/914—Transfer or decalcomania
Definitions
- the present invention relates to a new process for transferring azo dyes, which have a thiophene-based diazo component, from a support to paper coated with plastic with the aid of an energy source.
- a transfer sheet which contains a thermally transferable dye in one or more binders, optionally together with suitable auxiliaries, on a support, with an energy source, e.g. with a heating head, heated by short heating impulses (duration: fractions of a second) from the back, whereby the dye migrates from the transfer sheet and diffuses into the surface coating of a recording medium.
- an energy source e.g. with a heating head
- short heating impulses duration: fractions of a second
- EP-A-216 483 or EP-A-258 856 describes azo dyes which have diazo components based on thiophene and coupling components based on aniline.
- disazo dyes based on thiophene and aniline are known from EP-A-218 397 for this purpose.
- EP-A-302 628 teaches the thermal transfer of azo dyes which are derived from 2-aminothiophenes which have a condensed carbonyl group in ring position 5.
- the object of the present invention was to provide a method for transferring azo dyes, the dyes being intended to meet the above-mentioned requirements as well as possible.
- Residues Y in formula I are e.g. Ethylene, 1,2- or 1,3-propylene, 1,2-, 1,3-, 1,4- or 2,3-butylene, pentamethylene, hexamethylene or 2-methylpentamethylene.
- Suitable radicals R1, R2, R3, R4, R5 and R7 in formula I are e.g. Methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or tert-butyl.
- R1 and R4 are also, for example, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, 2-methylpentyl, heptyl, octyl, 2-ethylhexyl, isooctyl, nonyl, isononyl, decyl or isodecyl.
- Residues R1 are furthermore, for example undecyl, dodecyl, tridecyl, isotridecyl (the designations isooctyl, isononyl, isodecyl and isotridecyl are trivial drawings and come from the alcohols obtained after oxosynthesis - cf.
- R4 and R5 are also, for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy or sec-butoxy.
- Residues R4 are still e.g. Pentyloxy, isopentyloxy, neopentyloxy, hexyloxy, heptyloxy, octyloxy, 2-ethylhexyloxy, nonyloxy or decyloxy.
- Residues R5 are still e.g. Methylthio, ethylthio, propylthio, isopropylthio or butylthio.
- the dyes of the formula I are known from EP-A-201 896 or can be obtained by the methods mentioned there.
- the dyes transferred in the process according to the invention are generally distinguished by improved migration properties in the recording medium at room temperature, easier thermal transferability, higher photochemical stability, easier technical accessibility, better resistance to moisture and chemical substances, higher color strength , better solubility, higher color purity and higher thermal stability.
- the dyes are in a suitable organic solvent, for example chlorobenzene, isobutanol, methyl ethyl ketone, methylene chloride, toluene, tetrahydrofuran or their mixtures, processed with one or more binders, optionally with the addition of auxiliaries, to form a printing ink.
- a suitable organic solvent for example chlorobenzene, isobutanol, methyl ethyl ketone, methylene chloride, toluene, tetrahydrofuran or their mixtures
- binders optionally with the addition of auxiliaries
- binders All resins or polymer materials which are soluble in organic solvents and are capable of binding the dye to the inert support in an abrasion-resistant manner are suitable as binders. Preference is given to those binders which, after the printing ink has dried in air, absorb the dye in the form of a clear, transparent film, without any visible crystallization of the dye occurring.
- binders examples include cellulose derivatives, e.g. Methyl cellulose, ethyl cellulose, ethyl hydroxyethyl cellulose, hydroxypropyl cellulose, cellulose acetate or cellulose acetobutyrate, starch, alginates, alkyd resin, vinyl resin, polyvinyl alcohol, polyvinyl acetate, polyvinyl butyrate or polyvinyl pyrrolidone.
- Polymers and copolymers of acrylates or their derivatives, such as polyacrylic acid, polymethyl methacrylate or styrene-acrylate copolymers, polyester resin, polyamide resin, polyurethane resin or natural CH resin, such as gum arabic are also suitable as binders.
- Other suitable binders are e.g. in DE-A-3 524 519.
- Preferred binders are ethyl cellulose, ethyl hydroxyethyl cellulose or polyvinyl butyrate.
- the ratio of binder to dye preferably varies between 5: 1 and 1: 1.
- auxiliaries such as those specified in EP-A-227 092, EP-A-192 435 or the patent applications cited therein, are also suitable as auxiliaries, in addition, in particular organic additives which cause the transfer dyes to crystallize out during storage and when the ink ribbon is heated prevent, e.g. Cholesterol or vanillin.
- Inert carriers are e.g. Silk, blotting or glassine paper or plastic films with good heat resistance, e.g. optionally metal-coated polyester, polyamide or polyimide.
- the inert carrier is optionally additionally coated with a lubricating layer (slipping layer) in order to prevent the thermal head from sticking to the carrier material.
- a lubricating layer slipping layer
- Suitable lubricants are described, for example, in EP-A-216 483 or EP-A-227 095.
- the thickness of the dye carrier is generally 3 to 30 microns, preferably 5 to 10 microns.
- all temperature-stable plastic layers with affinity for the dyes to be transferred are suitable as the dye receiver layer. modified polycarbonate or polyester.
- Suitable formulations for the receiver layer composition are e.g. in EP-A-227 094, EP-A-133 012, EP-A-133 011, EP-A-111 004, JP-A-199 997/1986, JP-A-283 595/1986, JP- A-237 694/1986 or JP-A-127 392/1986 described in detail.
- the transmission takes place by means of an energy source, e.g. by means of a laser or by means of a thermal head which must be able to be heated to a temperature of ⁇ 300 ° C. so that the dye transfer can take place in the time range t: 0 ⁇ t ⁇ 15 ms.
- the dye migrates from the transfer sheet and diffuses into the surface coating of the recording medium.
- the polyester film (donor) containing the dye to be tested in the coating composition front side was placed with the front side on commercially available Hitachi Color Video Print Paper (recipient) and pressed.
- the encoder / receiver was then wrapped with aluminum foil and heated between two heated plates at different temperatures T (in the temperature interval 70 ° C ⁇ T ⁇ 120 ° C).
- the dyes mentioned in the following tables were processed according to A) and the resulting dye-coated carrier according to B) was tested for the transfer behavior.
- the tables show the thermal transfer parameters T * and ⁇ E T , the absorption maxima of the dyes ⁇ max (measured in methylene chloride) and the binders used.
Landscapes
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Thermal Transfer Or Thermal Recording In General (AREA)
Claims (3)
- Procédé de transfert de colorants azoïques sur un papier revêtu de matière plastique à partir d'un support, par diffusion à l'aide d'une source d'énergie, caractérisé en ce que l'on utilise un support sur lequel se trouvent un ou plusieurs colorants azoïques de formule IX représente un atome d'azote ou le reste C-CN,Z représente un atome d'oxygène ou le reste -CH(R⁷)-, R⁷ étant mis pour un atome d'hydrogène ou pour un groupement alkyle en C₁-C₄,R¹ représente un reste alkyle, alcanoyloxyalkyle, alcoxycarbonyloxyalkyle ou alcoxycarbonylalkyle, ces restes renfermant chacun jusqu'à 15 atomes de carbone et pouvant être substitués par des groupements phényle, (alkyl en C₁-C₄)phényle, (alcoxy en C₁-C₄)-phényle, halogénophényie, benzyloxy, (alkyl en C₁-C₄)benzyloxy, (alcoxy en C₁-C₄)benzyloxy, par un atome d'halogéne ou par un groupement hydroxy ou cyano, un atome d'hydrogène, un reste phényle éventuellement substitué par un groupement alkyle en C₁-C₁₅, alcoxy en C₁-C₁₅ ou par un atome d'halogéne, ou un reste de formule II
[-Y-O]m-R⁸ (II)
dans laquelleY est mis pour un reste alkylène en C₂-C₆,m est mis pour 1, 2, 3, 4, 5 ou 6 etR⁸ est mis pour un reste alkyle en C₁-C₄ ou pour un reste phényle eventuellement substitué par un groupement alkyle en C₁-C₄ ou alcoxy en C₁-C₄,R² et R³ sont identiques ou différents et représentent chacun, indépendamment l'un de l'autre, un atome d'hydrogène ou un reste alkyle en C₁-C₄,R⁴ représente un atome d'hydrogène, un reste alkyle en C₁-C₁₀, alcoxy en C₁-C₁₀ ou le reste -NH-COR² ou -NHSO₂R⁸, R² et R⁸ ayant chacun la signification donnée ci-dessus,R⁵ représente un atome d'hydrogène, de chlore, un reste alkyle en C₁-C₄, alcoxy en C₁-C₄, alkylthio en C₁-C₄ ou phényle éventuellement substitue par un groupement alkyle en C₁-C₄, alcoxy en C₁-C₄ ou par un atome d'halogène, etR⁶ représente un groupement cyano ou le reste -CO-OR¹, -CO-NHR¹ ou -CO-N(R¹)₂, R¹ ayant chaque fois la signification donnée ci-dessus. - Procédé selon la revendication 1, caractérisé en ce qu'il se trouve, sur le support, un ou plusieurs colorants azoïques de formule I dans laquelleR¹ représente un reste alkyle, alcanoyloxyalkyle ou alkyloxycarbonylalkyle, ces restes renfermant chacun jusqu'à 12 atomes de carbone et pouvant être substitués par des groupements hydroxy ou cyano, ou un reste de formule II
[-Y-O]m-R⁸ (II)
dans laquelleY est mis pour un reste alkylène en C₂-C₄,m est mis pour 1, 2, 3 ou 4 etR⁸ est mis pour un reste alkyle en C₁-C₄ ou pour un reste phényle éventuellement substitué par un groupement alkyle en C₁-C₄ ou alcoxy en C₁-C₄,R⁴ représente un atome d'hydrogène, un reste alkyle en C₁-C₆, alcoxy en C₁-C₆ ou le reste -NH-COR² ou -NHSO₂R⁸, R² et R⁸ ayant chacun la signification donnée dans la revendication 1,R⁵ représente un atome d'hydrogène, de chlore, un reste alkyle en C₁-C₄, alcoxy en C₁-C₄ ou phényle, etR⁶ représente un groupement cyano ou le reste -CO-OR¹, -CO-NHR¹ ou -CO-N(R¹)₂, R¹ ayant chaque fois la signification donnée ci-dessus. - Procédé selon la revendication 1, caractérisé en ce qu'il se trouve, sur le support, un ou plusieurs colorants azoïques de formule IaX représente un atome d'azote ou le reste C-CN,R¹ représente un reste alkyle en C₁-C₆ ou un reste de formule III
[-CH₂-CH₂-O]n-R⁸ (III)
dans laquellen est mis pour 1 ou 2 etR⁸ est mis pour un reste alkyle en C₁-C₄,R⁴ représente un atome d'hydrogène ou un reste méthyle, méthoxy ou (alcanoyl en C₂-C₅)amino etR⁶ représente un groupement cyano ou le reste -CO-OR¹, R¹ ayant la signification donnée ci-dessus.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4004600 | 1990-02-15 | ||
DE4004600A DE4004600A1 (de) | 1990-02-15 | 1990-02-15 | Verfahren zur uebertragung von azofarbstoffen |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0442360A1 EP0442360A1 (fr) | 1991-08-21 |
EP0442360B1 true EP0442360B1 (fr) | 1995-11-22 |
Family
ID=6400157
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP91101564A Expired - Lifetime EP0442360B1 (fr) | 1990-02-15 | 1991-02-06 | Procédé de transfert de colorants azoiques |
Country Status (4)
Country | Link |
---|---|
US (1) | US5145828A (fr) |
EP (1) | EP0442360B1 (fr) |
JP (1) | JPH05584A (fr) |
DE (2) | DE4004600A1 (fr) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE69215864T2 (de) * | 1992-07-14 | 1997-06-19 | Agfa Gevaert Nv | Thiazolylazoanilinfarbstoffe zur Anwendung in der thermischen Farbstoffsublimationsübertragung |
EP0581342B1 (fr) * | 1992-07-14 | 1997-01-02 | Agfa-Gevaert N.V. | Elément donneur de colorant pour le transfert thermique de colorants par sublimation |
ATE147018T1 (de) * | 1992-07-14 | 1997-01-15 | Agfa Gevaert Nv | Farbstoffdonorelement zur anwendung in der thermischen farbstoffsublimationsübertragung |
US5571765A (en) * | 1994-01-31 | 1996-11-05 | Agfa-Gevaert N.V. | Thermal dye transfer image with improved light-fastness |
EP0665117A1 (fr) * | 1994-01-31 | 1995-08-02 | Agfa-Gevaert N.V. | Image produite par transfert thermique de colorant, ayant une stabilité à la lumière améliorée |
GB9506117D0 (en) * | 1995-03-25 | 1995-05-10 | Ici Plc | Dye diffusion thermal transfer printing |
JP5829648B2 (ja) | 2013-06-11 | 2015-12-09 | 株式会社中部コーポレーション | 食材カッター |
CN109574880B (zh) * | 2017-09-29 | 2022-06-17 | 纳莹(上海)生物科技有限公司 | 一种荧光探针及其制备方法和用途 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB8521327D0 (en) * | 1985-08-27 | 1985-10-02 | Ici Plc | Thermal transfer printing |
DE3788072T3 (de) * | 1986-02-28 | 1997-02-20 | Ici Plc | Thermoübertragungsdruck. |
DE3630279A1 (de) * | 1986-09-05 | 1988-03-17 | Basf Ag | Verfahren zur uebertragung von farbstoffen |
DE3818404A1 (de) * | 1988-05-31 | 1989-12-07 | Basf Ag | Verfahren zur uebertragung von azofarbstoffen |
GB8817220D0 (en) * | 1988-07-20 | 1988-08-24 | Ici Plc | Thermal transfer printing |
-
1990
- 1990-02-15 DE DE4004600A patent/DE4004600A1/de not_active Withdrawn
-
1991
- 1991-02-05 US US07/651,455 patent/US5145828A/en not_active Expired - Fee Related
- 1991-02-06 DE DE59106925T patent/DE59106925D1/de not_active Expired - Lifetime
- 1991-02-06 EP EP91101564A patent/EP0442360B1/fr not_active Expired - Lifetime
- 1991-02-12 JP JP3018818A patent/JPH05584A/ja not_active Withdrawn
Also Published As
Publication number | Publication date |
---|---|
DE4004600A1 (de) | 1991-08-22 |
EP0442360A1 (fr) | 1991-08-21 |
JPH05584A (ja) | 1993-01-08 |
US5145828A (en) | 1992-09-08 |
DE59106925D1 (de) | 1996-01-04 |
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